Parasiticida



Remind Jan. 30, 1945 "UNITED STATES PABASITICIDAL PREPARATIONS Elbert c. we, Passaie, N. 1., assignor to United States Rubber Company. New York, N. Y" a corporation of New Jersey No Drawing. Original No. 2,362,564, dated November 14, 1944, Serial No. 485,886, May 6, 1943. Application for reissue December 9, 1944, Serial This invention relates to new and useful improvements in parasiticidal preparations. more particularly to germicides, thatis, fungicides and bacterieides, and to insecticides, the latter term being considered to include larvicides and arachnicides, as well as insectifuges and larvifuges. The invention further relates to methods of protecting organic material subject to attack by wtcroorganisms, as in the immunizing of seed, and the mildewprooflng of'fabrics and other material.

I have found that 2,2,4,6,6pentacl'iloro-4-cyclohexenedione-L3 is an effective germicide and insecticide. The structure oi-the compound may be representedas follows:

The graphic formula for the compound and method of preparation are described in Zincke and Rabinowitsch in Berichte, vol. 23, pages 3768 and It is there called pentachlor-m-diketo-R-hexen (the R stands for ring," meaning cyclo), and pentachlorresorcin.

Th 2,2,4,6,6-pentachloro-4-cyclohexenedione Lsmaybeusedasaseedprotectant andtoprotect plants or soil from organisms harmful to seeds and plants. It may also be applied toprevent or retard fungus growth and the formation of, for example, mildew on rope, wood, fur, hair,

feathers, cotton, wool, leather, rubber, rubberized healthy plants with an equal number of untreated seeds planted under the same conditions. Ob

,servations made at the end of ten days showed that 78% of the treated seeds had germinated and grownto healthy seedlings, whereas only 14% of the untreated seeds had germinated.

- Example II This case illustrates the effectiveness of 2,2,- 4,6,6- pentachloro4-cyclohexenedione-1,3 as a bactericide. chloroircy'clohexenedione-1,3 was s sp nded in water which contained 2% of Emulphor-EL (believed to be reaction product of fatty acid or fatty acid ester with ethylene oxide) as a dispersing agent. A section of potato was immersed in this suspension and allowed to stand at room temperature. No growth of naturally occurring bac term. was observed after thirty days. )n the other hand, a section of potato treated in a similar manner with a 2% solution of Emulphor-EL in water, which solution did not contain a germi cide, became heavily overgrown with naturally occurring bacteria within the same period of time.

Example HI The arachnicidal properties of 2,2,4,6,6-pentachloro-d-cyclohexenedione-lfi are shown by th following test: r

1 part by weight of 2,2,4,6,6-pentachloro-4- cyclohexenedione-1,3 was suspended in 200 parts .of water which contained A part of Nacconal or synthetic resin-coated fabrics, and the like.-

The 2,2,4,6,B-pentachloro-i-eyclohexenedhne-1Z3 may be applied as dust or sprays or in solution in a suitable solvent. It may be applied diluted or undiluted, or mixed with carrienor other fungicides, germicides or insecticides, fertilizers, hormones, buffering or safening agents. The following examples are given to illustrate cyclohexene-dione-lii in dust form. 'I"h'e seeds were then planted in soil known to befinfested ultimum. The eifectiveness of the fungicide was determined by comparing the number of treated lowing test:

4 pieces of woolen cloth 1%" 1': 4" were im- (wetting agent), The dispersion was .then

showed that 100% of the spiders had been killed while control plants which had been sprayed with water containing 25% of Nacconal but without the 2,2,4,6,6-pentaehloro 4-eyclohexenedione-1,3

showed 10% dead.

Example IV ro-4-cy'clohexenedione-13 are shown by. the folmersed in a 5% solution by weight of the chemical in acetone until saturated with the solution.

then removed, air-dried to remove the acetone,

' and each placed in a separate covered petri dish with a number of organisms, including Pwthium containing 5 black carpet beetle larvae, and a1- lowed to stand in a. dark place at room temperature m three weeks. Four similar pieces of unseeds which germinated and developed into t e t d woolen cloth were placedinseparate .5% by weight of 2,2,4,6,6-penta-. Y

sprayed on bean plants heavily infested with red I spiders. Counts taken 72 hours after spraying The repellent properties of awesome dishes, each containing five black carpet beetle larvae andthen allowed to stand for three weeks under equal conditions. At the end of this period it was found that no surface feeding hadoccurred on the treated samples, whereas very heavy feeding had. occurred on the untreated samples. I ur- I thermore, 100% of the larvae exposed to the treated samples were dead, whereas there was no mortality in the larvae 7 samples.

exposed to the untreated Having thus described my invention, what -I claim and desire to protect by letters Patent ia: 1. A fungicidal compositioncomprisinga carrier and 2,2,4,8,8-pentachloro-4-cyclohexenedione-1,3 as an essential active ingredient:

2. The method of protectingorgani materiel case? subject to attack by microorganisms which comprises said ornnicmaterial with 8,6-pentachloro-4-cvclohe2enediohe-13.

3; The method of protecting seeds, plants and soil, subject to attack by fungi, bacteria UdXR-R sects which comprise; treaties Seld mum: with ,4, -pentachloro-4-eyc1ohexenedione-1,3.

4. The method 'of immunizing seed which comrises treating said seed with2,2,4,6,6-pentachio- -rp-4-cyelohexenedione -1,3. 5. The method of controlling mildew on orc material which comprises treating said orhegenedione-IB. V

" EIBERT C. LADD.

sanic material'with 2,2,4,6,6-pentachloro-4-cyclo- 

